


carry on (from the start)

by bonnyappeteet



Category: Booksmart (2019)
Genre: 100 percent consensual though, Cunnilingus, F/M, House Party, Making Out, Safeword Use, Teacher-Student Relationship, Underage Drinking, Vaginal Sex, both parties are of age, other various house party activities, thigh riding
Language: English
Status: Completed
Published: 2019-06-09
Updated: 2019-06-09
Packaged: 2020-04-23 04:52:02
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,779
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19143934
Author URL: https://archiveofourown.org/users/bonnyappeteet/pseuds/bonnyappeteet
Summary: “You’re twenty, right?” came out before Stacy could even think about it much at all. Such a simple question, but the implications were.Well. She wasn’t really going to think about that too much now that she’d already asked the question, now was she?Besides:A. graduation was tomorrow,B. if she got caught, she was already screwed for being an adult — much less a teacher — at a party thrown by high schoolers, and,C. Theo’s slight nod, breathy “yeah”, and the slight disbelieving smile edging at his lips were enough to create a solid defense for herself.Okay.Again, Fuck.





	carry on (from the start)

**Author's Note:**

> title from “Make It Better” by Anderson .Paak.
> 
> oh man oh man i love this movie so much i saw it twice in three days. as much as the whole film captivated me, i fell for the theo/miss fine thing hard. i know the problematic nature of teacher/student relationships but look man, i’m a weak 18 year old who just got out of high school myself (lets go class of ‘19!! woo) and i have weak human kinks and i can only take so much of Olivia Wilde teasing us by pushing Jessica Williams and Eduardo Franco together in these situations, okay? sue me.
> 
> i will note that i wrote this originally calling Miss Fine “Jess” as that’s her actress’s first name and i couldn’t find her first name like anywhere at all (and who refers to themself internally as their last name? like nobody…) so I asked Olivia Wilde on instagram and sis replied??? oh my god i’m still shaking in my boots over it tbh... so we now know her name is in fact Stacy Fine, straight from the source. (btw Olivia if you’re reading this im so sorry for writing this mess, thank u for this gorgeous movie).
> 
> heres Olivia’s reply uwu: https://66.media.tumblr.com/58dcc66497a1b5ebdd90b619bcc8ec3d/tumblr_psreyybD7Y1rsojueo1_1280.jpg

Stacy Dianne Fine, try as she might, could not help herself from staring.

 

It was crazy and weird and so _wrong_ to see her students like this. All levels of fucked up, horny, hormonal teenagers were strewn throughout the room, making all kinds of chaos; they were draped across the muted-colored couches, standing against the patterned walls, sloppily launching ping pong balls into half-empty cups, or just straight-up making out in plain sight of (and some of them on top of) other partygoers.

 

_It_ is _graduation_ , Stacy supposed, taking another second to look around, _who am I to kill their fun?_

 

So she didn’t.

 

Instead, she did what she always did: she strolled into the corridor (as lowkey as possible — the last thing she wanted was some drunk kid calling unwanted attention to her), made herself a simple drink, found a warm corner (right near a fireplace that was _much_ nicer than any she’d seen at her own high school class’s house parties) and took a seat. There were beer cans everywhere, and her only view was of the many tens of drunk children surrounding her, but she didn’t mind so much at this point. She just needed a fucking _drink_.

 

It was nice to sit and observe, to be reminded of her life when she was their age just a few years ago and think of how far she’d come from that stifled eighteen year old. She knew if that girl could see her now she’d be judging the _shit_ out of her, but she also knew that she never had fun in high school — she never _let_ herself have fun back then.

 

_Where’s the harm in making up for lost time?_

 

* * *

 

 

Stacy wouldn’t say she was _surprised_ when Theo took a seat next to her by the fire, wide-eyed and clearly anxious. She wasn’t even startled by the coy look on his face as he spoke to her, voice hushed and mesmerised, _“Hi Miss Fine.”_

 

What shocked her more was how those eyes, that look, his voice — how _he_ — made her _feel_.

 

She’d glanced at him at the bar fooling around with the various drinks, mixing something up with practiced (if a bit clumsy) skill. She didn’t think much of it — he was one of Nick’s closest friends, so it was expected that he’d be trying to entertain guests.

 

Stacy just hadn’t realized that _she_ was now one of those guests too.

 

So if she sounded a bit taken aback when she replied, if her eyes were a little wider than usual, she’d just blame it on the drink (and a half (okay two (and another half))) that she’d already downed.

 

* * *

 

Theo wasn’t a slick fuckboy like most of the guys she’d had _feelings_ or _attraction to_ or _whatever the hell this was_ when she was in college.

 

(Really, he wasn’t —

 

her Freshman, Sophomore, and (regretfully) Junior years were full of guys like that — the ones who would say a few shitty lines, have her waking up sore in the morning, and could never seem to hold any kind of contact besides the occasional 2am “u up?” text. Those guys became a good resource when she needed to have a half-decent (okay, sometimes less than decent) fuck later on, but she certainly didn’t hold onto them much longer.

 

(She was coming up on 25 now, and those days were long behind her, though she was still single, and still managed to attract guys like that in bars, clubs, and nearly anywhere else they could find her. She was strong enough now to turn them down.

 

(Most of the time.)))

 

But Theo was genuinely _not_ one of those guys, and she could tell — he definitely hung out with some of them, and had the potential to be just as cruel as any of them, but he was… well, he was _soft._ He came to her nervous and genuinely out of breath, not with the mask of douchebag energy that insecure men so often put on before her.

 

No, Theo came baring a gift — a drink.

 

A delicious looking one at that.

 

Stacy, of course, ran through all the important points in her head:

_Are you too fucked up to make sane decisions?_ No.

→ _Does Theo look too fucked up to make sane decisions?_ No.

→ _Do you see powder in the glass?_ No.  

→ _Is your intuition telling you something's off?_ Hell fucking no.   

→ Drink that shit _now_.

 

It was a pale looking margarita, and Stacy couldn’t help the rush of warmth that chased up her back as she took a swig. It was perfect — the bitter colliding with the sweet, and the hot burn feeling familiar and _good_ as it went down.

 

“This is amazing,” she admitted, catching Theo’s gaze, which — oh. _Oh_.

 

And of course, coming from him, _“You’re amazing,”_ felt just as good as _“Hi Miss Fine,”_ had just a minute before.

 

_Fuck_.

 

* * *

 

“You’re twenty, right?” came out before Stacy could even think about it much at all. Such a simple question, but the implications were.

 

_Well_. She wasn’t really going to think about that too much now that she’d already asked the question, now was she?

 

Besides:

  1. graduation was tomorrow,
  2. if she got caught, she was already screwed for being an adult — much less a _teacher_ — at a party thrown by high schoolers, and,
  3. Theo’s slight nod, breathy _“yeah”,_ and the slight disbelieving smile edging at his lips were enough to create a solid defense for herself.



 

_Okay_.

 

_Again, Fuck_.

 

_Am I really about to do this?_

 

Stacy just rolled her eyes at herself, downed the rest of her drink, and stood with purpose.

 

“Come on,” she said, taking a few strides to out of their shared space and toward one of the connecting hallways.

 

“W-what?” Theo finally cracked, face disbelieving. Stacy tried to make her smile warm and sexy and not-too-obvious.

 

“Do you want to come with me?” she asked. “You don’t have to.”

 

He was already scrambling to his feet, mumbling softly whispered _yes yes yes-es_ and _oh my god’s_ trailing behind her quickly as she led him down the hall to a lamp-lit (and thankfully completely empty) bedroom. She took a few steps towards Theo, who was standing gawky in the middle of the room with his eyes wide and hands fiddling with one another, before sighing, stepping back towards the door, and turning the lock.

 

_Once again — Fuck_.

 

* * *

 

_Okay_ . _You can do this. Just talk to him and everything will be fine_.

 

“So, are we going to talk about this first, or-”

 

“Have you ever made love to a Mexican?”

 

Theo had said it so quickly that Stacy had a hard time processing his words, but she couldn’t help scoffing at them once they hit her.

 

“ _What_ now?”

 

His face quickly reddened as he sighed, pacing towards the bed and sitting on the edge of it, bringing his palms to cover his eyes. “I’m sorry, I’m so sorry, oh my god, I just feel so fucking… _weird?_ ”

 

Stacy took a few seconds to think about what he’d said, then carefully made her way over to the bed next to (but a respectful distance away from) him. “Bad weird?”

 

“I. I don’t think so. No, no, I’m just so fucking _nervous…_ You’re _Miss Fine_ and I’ve totally dreamt about this, but I never thought something like this would _actually_ happen, that you’d actually show up tonight,” He sighed, looking at the floor for a moment before chuckling lightly. “I am so fucking excited that you’re here, though.”

 

Stacy couldn’t help but laugh along with him. “I wasn’t planning on it. I just brought Molly and Amy here, they needed a ride.”

 

Theo startled at that, looking back from the floor to Stacy again. “Wait, those two are here? That’s fucking wild! I’ve never seen them out partying before.”

 

“Yeah, well, people do change.” She said, looking Theo in the eyes once more.

 

When she asked, “you’ve really dreamt about this?” he couldn’t help but tell the truth with a short nod and the heat rising even more fiercely to his cheeks.

 

When she asked “how often?” his half-baffled, half-guilty look gave it all away, and she couldn’t help but laugh.

 

This felt better, more free, exchanging words and glances and getting to see him smile.

 

* * *

 

Theo was _pretty_ , Stacy realized, and not just because of his hair.

 

Well, of course his hair, it was fucking _gorgeous_ , long and smooth but slightly crimped, like it had been entangled just moments before.

 

(And immediately questions like _What did it look like braided? Did he ever braid it? Could_ she _braid it for him?_ began to pop up in her mind, but those were thoughts for another time and another day or no time or day at all, oh my god Stacy Dianne you stop that right n-)

 

Theo was also pretty for his nose, his cheeks, his smooth skin, his pale pink lips, and _god_ those _eyes_ , deep brown and almost sleepy looking and puppy-dog-big.

 

Stacy had never noticed any of this before, but it was easy to notice it now that they were alone in the warm light, listening to the distant sounds of other people’s joy and their own mingling breaths.

 

She reached out a hand and laid it on his larger one, splayed out on the bed and supporting his weight as he leaned back. His breath hitched, his chest rising sharply as he looked at to her eyes, her cheeks, and her lips for confirmation.

 

When she asked, “is this your first time,” he shook his head, but followed it closely up with another statement because he wasn’t about to fuck this up with half-truths.

 

“First time with something like this, though. I don’t usually hook up, or anything like that. I have to actually like the person.”

 

She nodded. She knew what he meant.

 

* * *

 

Cycling through the important questions wasn’t hard at all with him. Theo was good at being honest.

 

“Do you feel drunk?” _“No, not really. I was watching the guys tonight, mostly.”_

“Are you sure you want to do this?” _“Hell yes. No, seriously,_ yes _. Full consent.”_

“How far do you want to go?” “ _As far as you want. As far as the night takes us.”_

 

The only one that tripped him up: “Do you have a safeword?”

 

Theo looked away and took a breath. “Uh, yeah I do… do you have one?” Stacy raised an eyebrow.

 

“Yes, I do. You first,” she smirked. Theo nodded, still looking bashful.

 

“It’s, uh, it’s Clefairy. The, uh, the Pokémon.”

 

Stacy managed to contain most of her laughter, but a few stifled giggled managed to slip out as she asked with feigned stoicism, “And how did you come up with that?”

 

Theo scratched his head shyly, laughing lightly as he explained, “Well, I was gonna use “Squirtle,” but I thought it sounded too sexy.”

 

Stacy couldn’t help but double over as she laughed out loud, and it felt _fucking good_.

 

* * *

 

They ended up agreeing on “Clefairy,” much to Theo’s initial disdain, because, in Stacy’s words, though he is a Shakespearean sprite, her usual safeword “Puck” just wasn’t nearly as funny.

 

“Are you sure about this?” Stacy asked one last time, her side comfortably pressed to the bed sheets as she lay beside Theo. She could tell he was more comfortable than ever, and both of them were getting tired of the formalities, but she had to try to keep this civil.

 

_“_ Yes _, Señora Fine.”_

 

Well, she was not expecting _that_.

 

His once-goofy smile had turned to a smirk, those wide eyes narrowing to focus on hers, and just like that she couldn’t even see the details of his _pretty_ fucking face anymore because their mouths were connecting in an urgent kiss.

 

It was a surprisingly good makeout, Stacy would think later looking back. It was, in a word, _hot_.

 

Theo’s breath was hot as he panted into her mouth, and he tasted reminiscently sharp like the tequila, and much to Stacy’s surprise and joy, he made little sounds, tiny moans and jolting gasps and occasionally soft growls, though he seemed not to be aware of them much at all.

 

She fucking _loved_ it.

 

Her jacket was already off, and she was unbuttoning his shirt as quickly as she could. It was a fucking ridiculous shirt, but he looked good in it. She loved bright clothes herself, which was clear from her own wardrobe, but she also gravitated towards others with them as well. But, as much as she liked Theo’s campy button-up, it really did have to go.

 

Her dress was the next issue, and Theo seemed to realize this as well as he abandoned his shirt, his eyes growing wide as he attempted to form the words necessary to ask her consent.

 

“I, well, can I-”

 

“Yes, Theo,” she said simply as she turned around, motioning for him to finish undoing the back. He struggled for a minute with the buttons at the top, but as soon as she felt the pressure of his hand dragging the zipper leave her back, she stood up and shed the garment.

 

Now, let’s be honest here, Stacy wasn’t exactly prepared for this tonight. This dress was one of the collection of sequined emergency party dresses she kept in her car, but her black t-shirt bra and gray panties were of the everyday variety; not to mention it’s not like she’d had any action for a while, so her downstairs wasn’t necessarily the _smoothest_.

 

As increasingly nervous as Stacy was becoming about those two issues (which she knew _should_ be non-issues since it was 20-fucking-19, but alas, she was not immune to propaganda or societal pressures so _sue her_ ) Theo did not seem phased at all; in fact, she considered that it was likely that his jaw could physically not have dropped with more speed or dramatic flair than it had once he saw her, so it seemed like she was in the clear.

 

Confidence returning, Stacy took her time on the way back to the bed. She turned around slowly and backed up to sit, motioning for Theo to stand up. He did, shucking off his shorts and hesitating at his boxers — toucan print, making Stacy giggle. He looked back to her at the sound. She moved to kneel on the bed, squinted playfully at him, and motioned with one finger for him to come close again.

 

Smiling, he returned, and he leaned down to meet her face in another long kiss as they laid down together. When he pulled away he kept his playful smile, leaning in close to her ear and letting out a raspy, trilled “Rrrrr!”

 

She didn’t really know how to react. It was funny, but somehow the jokiness of it made it even sexier to her, and she ended up cutting off her own laugh with a moan as he began to trail his mouth down her neck.

 

“Is - this - okay?” he asked between the nipping kisses from her jaw to her jugular and down further. She let out a low, sweet hum, confirming.

 

“Is _this_ okay?” she asked, tugging lightly at the hair starting at the base of his neck.

 

He had to pull his lips away from her collarbones with a _pop_ to let out another one of those surprised gasps. He let out a low “ _Si_ ,” as he ran his hands up her back, unhooking her bra and bringing his mouth to her left nipple, deep brown and pebbled from the stimulation.

 

She moaned, maybe a bit too loud.

 

As he worked her nipple with his mouth, his hands continued to move. With one hand he cupped her ass, her waist, her other breast, her thigh, then back to her ass, all while the other was making its way _down._

 

Stacy moaned at the feeling of his finger slowly rubbing her clit through her panties. She couldn’t help tugging even more needily at his hair and panting out “ _yeah, there_ ” — it just felt too damn good.

 

By the time Theo asked if she wanted to try anything else, she was already halfway to an orgasm, so after going to find a condom she returned to see him propped up with his back against the pillows. _Oh yeah_ , she thought _, I can work with this_.

 

Since Theo was already sitting up, Stacy threw the condom to the side and had him move to sit on some of the pillows stacked at the headboard, to which he quirked an eyebrow in confusion. She responded with a smirk and a “trust me,” which he obliged with a nod.

 

She smiled and quickly straddled his right thigh, making him gasp. The feeling of her pussy on him was _fucking divine_ , and Stacy? She was having a good fucking night.

 

_Fuck, that’s_ . _Wait._

 

“Up more, Theo. No like, sorry, put your leg down? Yeah, the angle needs to be u-u-up, oh my go-odd, _yeahbaby_.”

 

“Oh fuck, Señora, you’re s-oo fucking hot. Gonna cum, my queen?”

 

And fuck — the pleasure was surging through her, the warmth carrying up her spine and over her shoulders and through her chest, and the sheer _pressure_ of Theo on her clit feeling so, _so_ damn good — Stacy realized, the answer to that question could only be —

 

“Y-yes, yesss, ohmygod, fuck Theo, up and down a littlll-fuck _yeah_ move with it _fuck_ , fuck! Feels so good, so good baby, lemme cum _please, god, yeah!”_

 

Just coming down from that high felt _so_ good —

 

* * *

 

— and it felt just as good knowing Theo was there and ready for _more_. Also,

 

“Fuck, Theo did you call me your queen?”

 

Theo, too fucking hot to be bashful anymore, just nodded. “Like it?”

 

Stacy purred out a “yes”, leaning over to the bedside table and enjoying that Theo was leaning forward to take a good look at her ass.

 

“I’d say you could spank it, but that makes me get even louder and that’s just about the last thing we need right now.” Theo chuckled a bit and gave her ass a playful pinch which made her whine, but he was fucking hard and Stacy could see that, so she hurried up as she ripped open the condom wrapper and finally pulled his boxers down to reveal his length.

 

Stacy used Theo’s precum and her spit to get him ready, but she knew he wasn’t going to last forever so she made quick work of rolling it onto him and straddling his lap.

 

“You ready?” she asked for safety, and he replied a breathy “ _yes_ ” in a deep, needy voice.

 

Riding Theo was _amazing_ for both of them. His hands found purchase on her waist and made her feel supported in the best way. She would bounce wildly, locs falling in her face as she looked down at him and panted. She would sink down on his thick length and grind hard, his own hair strewn across his face as he hiked his hips up to meet hers, bringing his mouth to her chest to nip and lick here and there.

 

He didn’t last as short of a time as she thought, as she was nearing her own peak as well by the time he shuddered and warned her. All she did was sink down hard, nibbling at his ear and pressing her chest to his as he locked his arms behind her back and growled as he came.

 

As soon as his breathing calmed down to a normal level, he patted her thigh gently to signal her to dismount, as it were. She did, lying on her back on the other side of the bed, and after tying the condom up and tossing it god-knows-where in the room, Theo quickly moved himself down to the bottom of the bed so that his head was between Stacy’s legs. She was startled but pleased as he moved his fingers, then his mouth, to her folds, caressing and nipping and tugging and sucking in all the best ways. It didn’t take long at all for her to come like that, one hand tugging at his smooth hair as he locked eyes with her, his plump lips wrapped around her clit as she used her other hand to silence her scream of pleasure.

 

When he had cleaned her up and she was thoroughly spent, all she could do was look at him and sigh in contentment. He grabbed their respective pieces of underwear from across the room, and helped her dress as she was too blissed out to move much.

 

She thanked him with a few soft kisses and a shortlived post-coitus cuddle while she played with his hair, for which both of them were very grateful.  

 

* * *

 

It wasn’t long after that Stacy heard the other partygoers screeching and scrambling out the back (a sound she always listened for ever since her hardcore partying days) and rushed to put their clothes on. They made it out just in time (thank _god_ ), but got separated in the flurry of bodies.

 

Stacy walked back to her car alone, came home to an empty house, wrapped herself up in blankets and tried not to think of Theo all night long.

 

(And, _of fucking course_ , she was completely unsuccessful.)

 

* * *

 

“Morning, my Queen. So last night was amazing. Can I see you again?”

 

Despite the fresh embarrassment from disturbing Evelyn with her undignified growl and her internal conflict surrounding their encounter the previous night, the praise from Theo gave Stacy comfort.

 

Last night _was_ amazing. Of course she _wanted_ to see Theo again. She didn’t get _amazing_ all the time.

 

… But, he had his whole life ahead of him. A life full of mistakes, and successes, and everything that comes with being in your early 20’s. He was going to do so much, and he didn’t need some highschool crush bogging him down, not when he had a career at Google to look forward to. So instead of “ _yes_ ,” all she said was:

 

“Good luck at Google next year, kay?”

 

It was a good response. It was the responsible response. It was definitely the thing she was expected to say in this type of situation, and definitely the thing her 18 year old self would be proud of, and definitely the thing to keep her from doing something she’d regret.

 

… But, on her way back to the risers to watch the ceremony, she couldn’t help catching the glint in Theo’s eye. For a boy with such a goofy, pretty, puppy-dog face, Theo’s gaze was completely captivated and wise beyond his years, telling Stacy all she needed to know:

 

“Kay” _certainly_ wasn’t going to be the end of it.

  


**Author's Note:**

> pls do not be shy to add a comment or leave a request or idk tell me if i have errors?? really anything,, i've never really been good at this stuff omg,, thank u for reading ♡


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